(Z)-1-(3-Nitro-phen-yl)-2-(4-nitro-phen-yl)ethene.

In the mol-ecule of the title compound, C(14)H(10)N(2)O(4), the dihedral angle formed by the benzene rings is 53.66 (5)°. In the crystal structure, mol-ecules are linked into chains parallel to the [01] direction by inter-molecular C-H⋯O hydrogen-bonding inter-actions.

Related literature

For related literature, see: Boonlaksiri et al. (2000 ▶); Papper & Likhtenshtein (2001 ▶); Soto Bustmante et al. (1995 ▶). For the crystal structure of a related isomer, see: Chen & Cao (2007 ▶).

Experimental

Crystal data

C14H10N2O4

M = 270.24

Triclinic,

a = 7.2995 (13) Å

b = 8.0561 (11) Å

c = 11.831 (2) Å

α = 78.291 (7)°

β = 85.102 (7)°

γ = 67.536 (7)°

V = 629.53 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 (2) K

0.50 × 0.24 × 0.19 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.946, T max = 0.981

4608 measured reflections

2902 independent reflections

2009 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.138

S = 1.03

2902 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021077/rz2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021077/rz2231Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H10N2O4	Z = 2
Mr = 270.24	F000 = 280
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.2995 (13) Å	Cell parameters from 1175 reflections
b = 8.0561 (11) Å	θ = 3.5–27.2º
c = 11.831 (2) Å	µ = 0.11 mm−1
α = 78.291 (7)º	T = 296 (2) K
β = 85.102 (7)º	Block, yellow
γ = 67.536 (7)º	0.50 × 0.24 × 0.19 mm
V = 629.53 (18) Å3

Bruker SMART APEXII CCD diffractometer	2902 independent reflections
Radiation source: fine-focus sealed tube	2009 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 296(2) K	θmax = 27.9º
ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.946, Tmax = 0.981	k = −10→9
4608 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.066P)2 + 0.0698P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.138	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.24 e Å−3
2902 reflections	Δρmin = −0.19 e Å−3
182 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (7)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C11	0.4027 (2)	0.3521 (2)	0.95493 (13)	0.0408 (4)
C10	0.5246 (2)	0.2712 (2)	0.87050 (13)	0.0407 (4)
H10A	0.4941	0.3190	0.7930	0.049*
N2	0.2245 (2)	0.51528 (19)	0.92062 (12)	0.0491 (4)
O4	0.1303 (2)	0.59945 (18)	0.99507 (11)	0.0625 (4)
C9	0.6945 (2)	0.1168 (2)	0.90224 (13)	0.0418 (4)
C14	0.7294 (3)	0.0475 (2)	1.01961 (14)	0.0491 (4)
H14A	0.8396	−0.0581	1.0424	0.059*
C4	0.8254 (2)	0.2702 (2)	0.64805 (13)	0.0445 (4)
C1	0.7410 (2)	0.6180 (2)	0.52136 (13)	0.0437 (4)
N1	0.7019 (2)	0.8008 (2)	0.45317 (13)	0.0553 (4)
C12	0.4397 (3)	0.2862 (2)	1.07097 (14)	0.0509 (4)
H12A	0.3552	0.3448	1.1262	0.061*
O2	0.7283 (2)	0.91400 (19)	0.49721 (13)	0.0734 (4)
O3	0.1784 (2)	0.5610 (2)	0.81952 (12)	0.0804 (5)
C3	0.8289 (3)	0.4109 (2)	0.69887 (14)	0.0518 (4)
H3A	0.8598	0.3868	0.7767	0.062*
C6	0.7387 (3)	0.4823 (2)	0.46765 (14)	0.0490 (4)
H6A	0.7089	0.5071	0.3896	0.059*
C5	0.7812 (2)	0.3098 (2)	0.53140 (14)	0.0485 (4)
H5A	0.7803	0.2174	0.4957	0.058*
C2	0.7876 (3)	0.5846 (2)	0.63620 (14)	0.0509 (4)
H2A	0.7911	0.6773	0.6707	0.061*
C13	0.6048 (3)	0.1315 (3)	1.10274 (14)	0.0547 (5)
H13A	0.6326	0.0834	1.1805	0.066*
C8	0.8307 (3)	0.0184 (2)	0.81795 (15)	0.0511 (4)
H8A	0.8927	−0.1070	0.8429	0.061*
C7	0.8788 (3)	0.0810 (2)	0.71159 (15)	0.0531 (4)
H7A	0.9588	−0.0085	0.6709	0.064*
O1	0.6446 (3)	0.8324 (2)	0.35477 (12)	0.0854 (5)

	U11	U22	U33	U12	U13	U23
C11	0.0452 (9)	0.0352 (8)	0.0444 (8)	−0.0183 (7)	0.0008 (6)	−0.0066 (6)
C10	0.0452 (8)	0.0378 (8)	0.0383 (7)	−0.0167 (7)	−0.0026 (6)	−0.0025 (6)
N2	0.0481 (8)	0.0430 (8)	0.0556 (8)	−0.0150 (6)	0.0023 (6)	−0.0129 (7)
O4	0.0606 (8)	0.0543 (8)	0.0711 (8)	−0.0164 (6)	0.0168 (6)	−0.0256 (6)
C9	0.0439 (9)	0.0350 (8)	0.0457 (8)	−0.0163 (7)	−0.0029 (6)	−0.0018 (6)
C14	0.0525 (10)	0.0419 (9)	0.0503 (9)	−0.0207 (8)	−0.0091 (7)	0.0066 (7)
C4	0.0398 (8)	0.0452 (9)	0.0452 (8)	−0.0129 (7)	0.0074 (6)	−0.0104 (7)
C1	0.0399 (8)	0.0440 (9)	0.0449 (8)	−0.0156 (7)	0.0068 (6)	−0.0060 (7)
N1	0.0540 (9)	0.0489 (9)	0.0581 (9)	−0.0181 (7)	0.0067 (7)	−0.0047 (7)
C12	0.0675 (11)	0.0484 (10)	0.0420 (8)	−0.0291 (9)	0.0087 (8)	−0.0086 (7)
O2	0.0851 (11)	0.0496 (8)	0.0885 (10)	−0.0295 (7)	0.0047 (8)	−0.0130 (7)
O3	0.0746 (10)	0.0741 (10)	0.0590 (8)	0.0134 (8)	−0.0155 (7)	−0.0145 (7)
C3	0.0642 (11)	0.0569 (11)	0.0373 (8)	−0.0261 (9)	0.0041 (7)	−0.0105 (7)
C6	0.0498 (10)	0.0544 (10)	0.0416 (8)	−0.0181 (8)	−0.0002 (7)	−0.0095 (7)
C5	0.0512 (10)	0.0495 (10)	0.0476 (9)	−0.0185 (8)	0.0046 (7)	−0.0180 (7)
C2	0.0624 (11)	0.0497 (10)	0.0462 (9)	−0.0260 (8)	0.0092 (7)	−0.0157 (7)
C13	0.0726 (12)	0.0543 (10)	0.0384 (8)	−0.0311 (9)	−0.0056 (8)	0.0053 (7)
C8	0.0503 (10)	0.0353 (8)	0.0586 (10)	−0.0082 (7)	−0.0026 (8)	−0.0035 (7)
C7	0.0526 (10)	0.0427 (9)	0.0556 (10)	−0.0085 (8)	0.0078 (8)	−0.0129 (8)
O1	0.1193 (14)	0.0700 (10)	0.0582 (9)	−0.0343 (9)	−0.0165 (8)	0.0116 (7)

C11—C10	1.372 (2)	C1—N1	1.462 (2)
C11—C12	1.377 (2)	N1—O1	1.2150 (19)
C11—N2	1.467 (2)	N1—O2	1.218 (2)
C10—C9	1.392 (2)	C12—C13	1.374 (3)
C10—H10A	0.9300	C12—H12A	0.9300
N2—O3	1.2143 (18)	C3—C2	1.376 (2)
N2—O4	1.2209 (17)	C3—H3A	0.9300
C9—C14	1.393 (2)	C6—C5	1.371 (2)
C9—C8	1.470 (2)	C6—H6A	0.9300
C14—C13	1.378 (3)	C5—H5A	0.9300
C14—H14A	0.9300	C2—H2A	0.9300
C4—C5	1.389 (2)	C13—H13A	0.9300
C4—C3	1.397 (2)	C8—C7	1.328 (2)
C4—C7	1.473 (2)	C8—H8A	0.9300
C1—C2	1.376 (2)	C7—H7A	0.9300
C1—C6	1.378 (2)
C10—C11—C12	122.86 (15)	C13—C12—C11	118.13 (16)
C10—C11—N2	118.83 (13)	C13—C12—H12A	120.9
C12—C11—N2	118.31 (15)	C11—C12—H12A	120.9
C11—C10—C9	119.22 (14)	C2—C3—C4	121.34 (15)
C11—C10—H10A	120.4	C2—C3—H3A	119.3
C9—C10—H10A	120.4	C4—C3—H3A	119.3
O3—N2—O4	123.14 (15)	C5—C6—C1	118.73 (15)
O3—N2—C11	118.50 (14)	C5—C6—H6A	120.6
O4—N2—C11	118.35 (14)	C1—C6—H6A	120.6
C10—C9—C14	117.92 (15)	C6—C5—C4	121.50 (15)
C10—C9—C8	122.99 (14)	C6—C5—H5A	119.2
C14—C9—C8	118.99 (15)	C4—C5—H5A	119.2
C13—C14—C9	121.71 (16)	C3—C2—C1	118.52 (16)
C13—C14—H14A	119.1	C3—C2—H2A	120.7
C9—C14—H14A	119.1	C1—C2—H2A	120.7
C5—C4—C3	117.99 (15)	C12—C13—C14	120.13 (15)
C5—C4—C7	119.46 (15)	C12—C13—H13A	119.9
C3—C4—C7	122.43 (15)	C14—C13—H13A	119.9
C2—C1—C6	121.91 (15)	C7—C8—C9	129.92 (15)
C2—C1—N1	119.00 (15)	C7—C8—H8A	115.0
C6—C1—N1	119.03 (15)	C9—C8—H8A	115.0
O1—N1—O2	123.13 (16)	C8—C7—C4	130.11 (16)
O1—N1—C1	118.13 (16)	C8—C7—H7A	114.9
O2—N1—C1	118.75 (15)	C4—C7—H7A	114.9
C12—C11—C10—C9	−0.7 (2)	C7—C4—C3—C2	176.81 (16)
N2—C11—C10—C9	179.75 (13)	C2—C1—C6—C5	1.0 (3)
C10—C11—N2—O3	8.4 (2)	N1—C1—C6—C5	178.16 (14)
C12—C11—N2—O3	−171.23 (16)	C1—C6—C5—C4	0.2 (3)
C10—C11—N2—O4	−171.07 (14)	C3—C4—C5—C6	−1.1 (2)
C12—C11—N2—O4	9.3 (2)	C7—C4—C5—C6	−177.24 (16)
C11—C10—C9—C14	2.1 (2)	C4—C3—C2—C1	0.4 (3)
C11—C10—C9—C8	178.34 (14)	C6—C1—C2—C3	−1.3 (3)
C10—C9—C14—C13	−2.3 (2)	N1—C1—C2—C3	−178.45 (16)
C8—C9—C14—C13	−178.65 (16)	C11—C12—C13—C14	0.6 (3)
C2—C1—N1—O1	−173.84 (17)	C9—C14—C13—C12	0.9 (3)
C6—C1—N1—O1	8.9 (2)	C10—C9—C8—C7	32.4 (3)
C2—C1—N1—O2	6.3 (2)	C14—C9—C8—C7	−151.46 (19)
C6—C1—N1—O2	−170.93 (15)	C9—C8—C7—C4	6.1 (3)
C10—C11—C12—C13	−0.8 (3)	C5—C4—C7—C8	−140.7 (2)
N2—C11—C12—C13	178.83 (14)	C3—C4—C7—C8	43.3 (3)
C5—C4—C3—C2	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1i	0.93	2.56	3.388 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1i	0.93	2.56	3.388 (2)	149

Symmetry code: (i) .